Although the city gets a bad rep for its bitter winters and Windy City misnomer, there is no shortage of indoor things to do in Chicago on a cold or rainy day. Whether you’re traveling with kids, on a romantic weekend away, or painting the town on a girls trip in Chicago, there is something for everyone on this list.
Garfield Park or Lincoln Park Conservatory
Take the flora and fauna of the outdoors inside, and explore the five houses that make up the Garfield Park Conservatory. Even on a cold or rainy day in Chicago, you can be quickly transported into a desert oasis and tropical landscape. Reservations are free, with an optional donation. Book your reservation online up to two weeks in advance.
If your hopes of spending the day in Lincoln Park are rained out, pivot your plans and head to the Lincoln Park Conservatory. The Lincoln Park Conservatory is located in Lincoln Park, just north of the zoo. Entrance is free, with optional donations encouraged. Book a free reservation online to ensure a spot on weekends. If you find yourself unexpectedly caught in the rain, walk-ins can also typically be accommodated.
Music Box Theater
Music Box Theater is the beacon of Lakeview’s Southport Corridor. The iconic venue has retained its original character and design since it opened in 1929. Although it’s known as a home for independent and foreign films, you can often catch a comfort class, like the annual showing of It’s a Wonderful Life each December.
Spa Day at Aire
Aire Ancient Baths is not your average spa-day. As you enter the unassuming West Town location, the buzz of the city fades away and you are transported into a candle-lit dream state. Among the many various pools and steam rooms, the most transcendent of all is the float pool, where the salinity matches that of the dead sea. While weightlessly floating, you lose track of all space and time. The only thing to bring you back to reality are the chimes that sound to indicate when your time is up.
As one of only two locations in the U.S., Aire is the best thing to do on a cold or rainy day in Chicago. To ensure an intimate experience for all guests, reservations are limited each hour. Experiences book up weeks in advance, so plan your afternoon at Aire as soon as you can.
Play Bar Games
Chicago is home to many bars with a playful twist. From board games to indoor lawn games, arcade classics to kicked up bar games. There is something for everyone looking to kick up the competition.
- Darts at Point & Feather
- Darts at Flight Club
- Ping Pong at Spin
- Ping Pong at Ace Bounce
- Bocci and Billiards at The Game Room
- Shuffleboard at Royal Palms
- Arcade Games at Replay Lincoln Park
- Board Games at Guthries Tavern
Visit Museums
At the risk of stating the obvious, I must say, Chicago has incredible museums. I know you may be thinking, duh, but there is a reason the city’s museums are on every list of things to do in Chicago on a cold or rainy day.
While the Art Institute and Field Museum are the best known, they may be overcrowded on a bitterly cold winter day in Chicago. Instead, head to some of the lesser trafficked museums like the DuSable Museum of African American History or the Chicago History Museum.
Top Golf Swing Suite
In lieu of driving an hour to the closest Top Golf, head to the Top Golf Swing Suite. The Top Golf simulator is hidden within the 900 North Michigan Shops, making it a great indoor activity in Chicago to round out an afternoon of high end shopping. The curated menu offers more than your typical mall food, with options from Small Cheval, the famed Au Cheval’s fast casual spin-off.
See a Broadway Show
Chicago has a lively theater scene that often gets the best of Broadway. Every national tour stops in the Windy City, and there is always something on. You may even get a chance to catch a world-premiere of a show before it hits New York’s Broadway. Chicago is often a test market for pre-Broadway debuts. Kinky Boots, On Your Feet!, and more, have all shared the same Chicago to New York pattern before going on to win best new musical Tony awards.
While it’s not easy to predict the weather, a Broadway show is a great thing to do on a cold or rainy day in Chicago. To score last minute tickets, try hitting the box office when it opens in advance of showtime. Tickets aren’t guaranteed, but you can often score great seats without the online fees if your schedule is flexible.
Check out Broadway in Chicago for a list of what’s on and upcoming.
Intimate Dining
When patios close for the winter, Chicago trades al fresco dining for cozy interiors. Chicago is a foodies’ paradise, so it’s no surprise that one of the best indoor things to do in Chicago is to warm up over a meal. Some restaurants with the most intimate atmospheres are:
- Geja
- Armitage Ale House
- Ciccio Mio
- Wilde
- Gilt Bar
- Frontier
- High Five Ramen
- Ada Street
Chicago Magic Lounge
Chicago Magic Lounge is a hidden gem that’s quite literally hidden behind a false laundromat facade. The city has a longstanding history of comedy, but a lesser-known magical past. This speakeasy-style magic lounge pays homage to the “Chicago-Style” close up magic that exploded in the city in the early 1900s. You’ll be enchanted by close up, table side tricks before the main show begins, and guaranteed to be entertained by the main stage. Book your tickets online in advance, as shows fill up quickly.
Get Cozy at Speakeasy
When it’s too cold or dreary to be outside, get cozy in one of the city’s many hidden speakeasies. The Office is hidden in Fulton Market beneath The Aviary, Chicago’s most renowned cocktail experience. The Office is a more approachable, but no less impressive, cocktail bar by the Alinea Group. It’s an intimate vibe that can accommodate reservations of up to 6 guests. Due to the intimate nature, there is limited capacity and reservations are required in advance.
Other speakeasies worth checking out are:
- The Violet Hour (Wicker Park)
- The Drifter at Green Door Tavern (River North)
- Booze Box (West Loop)
- The Library at Gilt Bar (River North)
- Blind Barber (Fulton Market)
What is your favorite thing to do in Chicago when it’s cold or rainy? Comment below with your winter favorites!
